Objectives With increased bicycle use during the COVID-19 pandemic and growing availability of bicycle-sharing programs in Montreal, we hypothesize helmet use has decreased. The aim of this study was to evaluate helmet use and proper fit among Montreal cyclists during the pandemic relative to historical data. Methods Nine observers collected data on bike type, gender, helmet use, and ethnicity using the iHelmet© app at 18 locations across the island of Montreal from June to September 2021. Proper helmet wear was assessed at one busy location. Multiple logistic regression was used to identify factors associated with helmet wear and results were compared to a historical study. Results Of the 2200 cyclists observed, 1109 (50.4%) wore a helmet. Males (OR = 0.78, 95%CI = 0.65–0.95), young adults (OR = 0.65, 95%CI = 0.51–0.84), visible minorities (OR = 0.38, 95%CI = 0.28–0.53), and bike-share users (OR = 0.21, 95%CI = 0.15–0.28) were less likely to be wearing a helmet, whereas children (OR = 3.92, 95%CI = 2.17–7.08) and cyclists using racing bicycles (OR = 3.84, 95%CI = 2.62–5.62) were more likely to be wearing a helmet. The majority (139/213; 65.3%) of assessed cyclists wore properly fitting helmets. Children had the lowest odds of having a properly fitted helmet (OR = 0.13, 95%CI = 0.04–0.41). Compared to 2011, helmet use during the pandemic increased significantly (1109/2200 (50.4%) vs. 2192/4789 (45.8%); p = 0.032). Conclusion Helmet use among Montreal cyclists was associated with age, gender, ethnicity, and type of bicycle. Children were least likely to have a properly fitted helmet. The recent increase in popularity of cycling and expansion of bicycle-sharing programs reinforce the need for bicycle helmet awareness initiatives, legislation, and funding prioritization.